The present invention relates to acrylate esters of 1,1,1-trishydroxyphenylethane (THPE) or more particularly to mono-, di-, and triacrylated esters of THPE. The invention also relates to a process for their preparation, their use as multifunctional polymerizable monomers, and homo- and co-polymers produced therefrom. Such compounds find use in the production of protective coating compositions, adhesives, photosensitive compositions, and the like.
Acrylate esters of 1,1,1-trishydroxyphenylethane may be produced by reacting 1,1,1-tris(4'-hydroxyphenyl)ethane with an acrylating agent as hereinafter described. It is known in the art that the intermediate 1,1,1-tris(4'-hydroxyphenyl)ethane may be produced by reacting 4-hydroxyacetophenone with phenol. Typically this is performed with phenol also used as the solvent for the mixture. THPE itself may be produced according to a method described in U.S. Pat. application No. 07/478,072, filed Feb. 9, 1990, now U.S. Pat. No. 4,992,598 which is incorporated herein by reference. According to that disclosure, very pure THPE is obtained by washing a crude reaction mixture of 4-hydroxyacetophenone and phenol with a THPE saturated wash/methanol liquid prior to a recrystallization. It has been found that by use of such a wash yields of pure white THPE are good, and solvents have a more productive use. As a result of the process, most of the color bodies are removed in the wash stage where the color of the crude THPE changes from a dark rusty color to a light tan. The balance is removed in the recrystallization. With crude THPE washed with recycled recrystallization filtrate, only a single recrystallization from methanol/water is necessary to meet white color and high purity requirements. This recrystallization is basically a precipitation of THPE from the methanol/water solution. By acrylating THPE, one produces the inventive monomeric mono-, di-or tri-acrylate esters of 1,1,1-trishydroxyphenylethane. These may be polymerized, copolymerized and/or crosslinked by the use of known free radical polymerization and crosslinking techniques.